Azo dyestuffs and process for the manufacture of same



Patented Aug. 12, 1924.

UNITED; STATES PATENT OFFICE.

HERMANN FRITZSCHE AND Emir. nnnnn, or BASEL, SWITZERLAND, ASSIGNOBS 'ro SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF BASEL, SWITZERLAND.

AZO DYESTUFFS AND PROQESS FOR THE MANUFACTURE OF Sm No Drawing.

To all whom it may concern:

Be it known that we, HERMANN Fnrrzsorrn and Earn. llnenn, both citizens of the Swiss Republic, and residing at Basel, Switzerland, have invented new and useful Azo I Dyestuffs and Processes for the Manufacture of Same, of which the following is a full. clear, and exact specification.

The present invention relates to new 10 pyrazolone dyestuffs which are of much importance for the production of uniform and fast tints on the fiber. The invention comprises the dyed fabrics or other materials,

wherein R signifies an 1-aryl-5-pyrazolone which contains an sO NH -group in its aryl nucleus, and R an aryl nucleus. These new azo dyestuffs form yellow to brown and red-brown powders, soluble in water to yellow to orange solutions. They dye wool in an 'acid bath in very uniform yellow to brown tints. If an o-oxydiazo compound has been chosen as a diazocom ound the acid wool dyeings obtainable, w en afterchromed, change to orange to blue-red tints of great purity which are fast to fulling and 40 to potting.

The following examples illustrate the invention without, however, limiting the same.

Example 1.

The diam-compound prepared in the usual manner from 173 parts of 2-amino-1-benzenee sulfonic acid is introduced into an aqueous solution containing 285 parts of 1- (3 sulfamido) -pl1enyl-5 pyraz'olone 3 carboxylic acid and an excess of sodium carbonate. The product is a yellow dyestuif which is filtered after addition of a little common salt. It forms a yellow powder dissolving Application filed October s, 1923. Serial no. 687,407;

in water to a yellow solution; it dyes wool in an acid bath beautiful greenish-yellow tints, very fast to light and very uniform.

If in this example, 5-methyl-2-amino-1- benzenesulfonic acid be substituted for the 2-amino-1-benzenesulfonic acid, there is obtained a golden-yellow dyestufi of like properties. 4

I E :mmplc 2?.

225 parts of 2-aminonaphthalene-l-sulfonic acid aredissolved in the usual manner and to tlf solution is added the dlazocompound obtained in an aqueous solution containing 255 parts of 1-(3-sulfamido-6- methyl) -3-methyl-5-pyrazolone and an excess of sodium carbonate. To the new dyestuflt' thus formed there is-added a little common salt and it is filtered and-dried. It then forms an orange-powder which dissolves in water to a yellow solution and dyes wool in an acid bath beautiful golden-yellow tints which are excellently uniform and of good fastness to light;

The analogous dyestulf prepared from the diazo-compound of 4-aminobenzene l-sulfonic acid dyes wool yellowish-green tmts.

Eaiample 3.

Ewample 4.

272 parts of the sodium salt of the (HMO- compound of 1-amino-2-oxynaphthalene-4- sulfonic' acid are introduced into a cooled solution of 253 parts of 1-(3'-sulfamido) phenyl-3-inethyl-5-pyrazolone in caustic soda. of 30 per cent strength. The mixture is stirred for some hours and mineral acid. The new dyestufi is filtered and may be purified by crystallization from water. It is a brick-red powder which disprevious example p the dyestuff. then isolated by acidifying slightly with a o-wder soluble in water to an orange ion solves in water to an orange solution, becoming more orange on addition of caustic soda. It dyes wool in an acid bath orange-brown tints which by after-chroming yield a pure blue-red, very fast.

By substituting in this exam ile for. the 1- (3'-sulfamido) -phenyl-3-methy -5-pyrazolone, another aryl-3-methyl-pyrazolone contaifniing a sulfamido group in the arylnucleus an analogous result is obtained,

while if the corresponding arylpyrazolone-3- carboxylic acids are used the tints of the dyestuffs are notably more blue-red;

Example 5.

295 parts of the nitrated dia-zo-compound of 1-amino-2-oxynaphthalenel-sulfonic acid are introduced into a cool solution of 253 arts of 1-(3'-sulfamido)- phenyl-3-meth -5-pyrazolone and 50 parts of sodium carbonate in about 130 parts of water. The whole is stirred for some hours and the dyestuff then isolated by slightl acidifying the mixture with a mineral aci The new dyestufi is then filtered. It may be purified by crystallization from water. It is a brown powder, soluble in water to an orange-brown solution becoming orange on addition of caustic soda. It (1 es wool in an acid bath. brown tints which y afterchroming become a very fast red.

. What we claim is:

1. The herein described new azo d estufis which correspond with the general ormula wherein R signifies a 1-aryl-5-pyrazolone which contains an SOJTH group in its aryl nucleus,and R an aryl nucleus, which dyestufi's constitute yellow to red-brown and I brown powders soluble in water to yellow tints.

to orange solutions,

dyeing wool from an acld bath very uniform yellow to brown 2. The herein described new azo dyestuffs which correspond with the general formula r RN= NR' wherein R signifies a 1-aryl-5 -pyrazolone which contains an SO NH up in its aryl nucleus, and R a monosu fonated aryl nucleus, which dyestuffs constitute yellow to red-brown and brown powders soluble in water to yellow to orange solutions, dyeing wool from an acid bath very uniform ye low to brown tints.

3. The hereindescribed new azo dye- 6 stufi'swhich correspond with the general b1 wherein R signifies a 1-a 1-5- razolone which contains an 80 N53 d p in its arylnucleus and R a monosu fonated aryl more very fast to fulling and to nucleus which contains an OH roup in ortho-position to the azo bridge, w ich dyestuffs constitute red-brown to brown powders soluble in water to orange to brownorange solutions which change to yellow to orange on addition of alkalies, dyeing -Wool in an acid bath very uniform yelloworange to brown tints which, by afterchroming, become orange to blue-red, the dyeing being very fast to fulling and to pottin 4. Tie herein described new azo dye- .stufi's which correspond with the general formula R-NzN-R wherein R signifies a l-aryl-3-methyl-5-T which correspond with the general ormula' R-N=NR' wherein R si pyrazolone w ich contains an S0, group in its aryl nucleus, and R a 2-0xynaphthalene--sulfonic acid nucleus where the azo bridge adheres to the ition 1- of the naphthalene nucleus, whic dyestufis constitute red-brown to brown powders soluble in water to orange to brown-orange solutions which become more yellow and more pure on addition of alkalies, dyeing wool in an acid bath very uniform brown to orange tints which, by after-chroming, become red to blue-red, the dyeings being very fast to fulling and to potting.

6. The herein described new azo d estufis which correspond with the general ormula wherein R signifies a 1(3'-sulfamido)-aryl- 3-methyl-5-pyrazolone, and R a 2-oxynaphthalene-4-sulfonic acid nucleus where the azo bridge adheres to the osition 1- of the naphthalene nucleus, w ich dyestuffs constitute red-brown to brown 'owders solue' in Water to orange to rown-orange solutions which become more ellow and pure on addition of alkalies, dyeing wool in an acid bath very uniform brown to orange tints which, by after-chroming, becomered to blue-red, the dyeings being potting.

-ing--w0ol in an acid bath ve 7. As new prcduct the herein described new azo dyestufi' which corresponds with the formula constituting a brown-red powder soluble in water to an oran e solution which becomes v claim 1.

' 9. .Material dyed with the dyestufis of claim 2.

10. Material dyed with the dyestnfis of claim 3.

claim 4.

12. Material dyed with the dyestuflfs of 25- claim 5.

- 11. Material dyed with the dyestuffs of 13. Material dyed with the dyestufis of claim 6.

14:. Material dyed with the dyestuffs of claim 7.

In witness whereof we have ereuntc signed our names this 27th day 0; September 1923,in the presence of two subscribing witnesses.

EMIL REBER.

Witnesses: AMAND BRAUN, Josnrm Swmmm HERMANN FRITZSCHE. 

